Trans-2,3,13,14-tetradehydro-9-deoxy-9-methylene-PGF compounds

ABSTRACT

The present specification relates to novel 9-deoxy-9-methylene-trans-2,3-didehydro-PGF compounds with improved pharamcological properties. While these compounds are useful in inducing a wide variety of prostaglandin-like pharmacological effects, they are specifically useful as regulators of procreation and fertility.

The present application is a divisional application of Ser. No. 893,771, filed 5 Apr. 1978, now U.S. Pat. No. 4,165,436, issued 21 Aug. 1979.

The present invention relates to prostaglandin analogs, for which the essential material contituting disclosure therefor is incorporated by reference here from U.S. Pat. No. 4,165,436. 

I claim:
 1. A prostaglandin analog of the formula ##STR1## wherein m is one to 5, inclusive; wherein Y₂ is --C.tbd.C--;wherein M₁ is ##STR2## wherein R₅ is hydrogen or methyl; wherein L₁ is ##STR3## wherein R₃ and R₄ are hydrogen, methyl, or fluoro, being the same or different, with the proviso that one of R₃ and R₄ is fluoro only when the other is hydrogen or fluoro; wherein g is 4, 5, or 6; wherein R₁ is hydrogen, alkyl of one to 12 carbon atoms, inclusive, cycloalkyl of 3 to 10 carbon atoms, inclusive, aralkyl of 7 to 12 carbon atoms, inclusive, phenyl, phenyl substituted with one, two, or three chloro or alkyl of one to 3 carbon atoms, inclusive, or a pharmacologically acceptable cation.
 2. A prostaglandin analog according to claim 1, wherein m is
 3. 3. A prostaglandin analog according to claim 2, wherein g is
 4. 4. A prostaglandin analog according to claim 3, wherein at least one of R₃ and R₄ is fluoro.
 5. 9-Deoxy-9-methylene-16,16-difluoro-trans-2,3,13,14-tetradehydro-PGF₁, a prostaglandin analog according to claim
 4. 6. A prostaglandin analog according to claim 3, wherein at least one of R₃ and R₄ is methyl.
 7. 9-Deoxy-9-methylene-16,16-dimethyl-trans-2,3,13,14-tetradehydro-PGF₁, a prostaglandin analog according to claim
 6. 8. 9-Deoxy-9-methylene-16,16-dimethyl-trans-2,3,13,14-tetradehydro-PGF₁, methyl ester, a prostaglandin analog according to claim
 6. 9. A prostaglandin analog according to claim 3, wherein R₃ and R₄ are both hydrogen.
 10. A prostaglandin analog according to claim 9, wherein R₅ is methyl.
 11. 9-Deoxy-9-methylene-15-methyl-trans-2,3,13,14-tetradehydro-PGF₁, a prostaglandin analog according to claim
 10. 12. A prostaglandin analog according to claim 9, wherein R₅ is hydrogen.
 13. 9-Deoxy-9-methylene-trans-2,3,13,14-tetradehydro-PGF₁, methyl ester, a prostaglandin analog according to claim
 12. 14. 9-Deoxy-9-methylene-trans-2,3,13,14-tetradehydro-PGF₁, a prostaglandin analog according to claim
 12. 